Ethyl Acetate → Butyl 4-((3,4-diaminophenoxy)methyl)piperidine-1-carboxylate

Participants

Reaction Steps

tert-Butyl 4-((4-amino-3-nitrophenoxy)methyl)piperidine-1-carboxylate (3.58 g, 10.18 mmoles,) was dissolved in ethyl acetate (60 ml) and methanol (40 ml). The solution was treated with 600 mg of 10% palladium on carbon (50% water w/w). The slurry was then shaken on a Parr hydrogenator and treated with a 40 psi of hydrogen gas, at room temperature. After 16 hours, the slurry was filtered through a plug of Celite, which was subsequently washed with ethyl acetate (50 ml) and methanol (50 ml). The resulting filtrate was then evaporated at reduced pressure to give 3.42 g of tent-butyl 4-((3,4-diaminophenoxy)methyl)piperidine-1-carboxylate (100% yield). The material was used in the next step without any further purification. 1H-NMR (400 MHz, DMSO-d6) δ 8.40 (s, 1H), 7.49 (d, 1H), 7.24 (d, 1H), 5.32 (br s, 4H), 3.82 (d, 2H), 3.65 (m, 2H), 2.40 (s, 3H), 1.76 (m, 1H), 1.54 (m, 2H), 1.38 (s, 9H), 0.98 (m, 2H). MS (EI): 322 (MH+).

Provenance & Evidence